20 Of ‘Playboy’ And Hugh Hefner’s Most Iconic Moments

Both good and bad

Iconic is a vastly overused phrase, don’t you think? Not everything or everyone is deserving of the label. However, Hugh Hefner—and the legacy he left as the founder of Playboy—is. As divisive of a figure as he might have been, Hefner contributed a lot to our culture, in ways both good and bad.

There’s a running joke that nobody reads Playboy for the articles, but the magazine published some of the best writers of its time. Everyone from Gabriel Garcia Marquez to Margaret Atwood to Roald Dahl to Jack Kerouac contributed to issues, while fascinating interviews with James Baldwin, Miles Davis, Bette Davis, Steve Jobs, Malcolm X, Martin Luther King, Jr., John Lennon, and Yoko Ono spanned the pages.

Whether we’re talking about Hefner as a leader in the sexual revolution or a “sadistic pimp,” the evolving magazine, or the famed Playboy Mansion, there is, for sure, a lot to talk about. Ahead, we round up 20 of the most iconic moments you should know about.

4. Hugh Hefner giving late comedian Dick Gregory his big break: "You had a courage when no one was bringing in blacks and minorities, and let you stand flat-footed in America and just talk, you brought me in," Gregory told Hefner during a 2001 Comedy Central roast (he was being sincere, despite the usual purpose of the show). "You didn't give me a lecture. You gave me no instructions."

11. Margaret Atwood’s “The Bog Man” essay:It tells the story of a woman named Julie who discovers the 2,000-year-old body of a man as she learns of her partner's cheating ways.

12. That awful John Mayer interview:He delivers lines like: "Someone asked me the other day, 'What does it feel like now to have a hood pass?'" and, says of Jessica Simpson, "That girl is like crack cocaine to me... Sexually it was crazy. That's all I'll say. It was like napalm, sexual napalm."